How many flights depart from Region of Ontario to Chicago on average per week?

556 flights are operational weekly from Region of Ontario to Chicago as of January 2026. The most popular departure day for this route is Wed, with 15% of flights per week taking off on this day.

How many flights depart from Region of Ontario to Chicago on average per day?

79 flights are operational daily from Region of Ontario to Chicago as of January 2026. The most popular departure time for this route is 6:00a.m., with 50% of flights per day taking off at noon.

How long does it take to fly to Chicago?

Flight times from Region of Ontario to Chicago vary, but if you’re flying out of Ottawa and flying into Chicago O'Hare Intl Airport (one of the most popular routes), then the duration is 2h 08m on average. Another popular route from Region of Ontario to Chicago is flying from Toronto to Chicago O'Hare Intl Airport, which will take roughly 5h 11m. Keep in mind that layovers or delays could extend your travel time.

Which airlines fly to Chicago?

Air Canada, United Airlines and Porter Airlines are the top three most popular airlines that fly to Chicago from Region of Ontario according to our data. Air Canada is the first choice among our users, with 58% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Ontario to Chicago?

Porter Airlines, Air Canada, and United Airlines are the most popular carriers operating from Ontario to Chicago

When did momondo last update prices for flights from Ontario to Chicago?

Prices for flights from Ontario to Chicago were last updated today.

How many operators does momondo search for flights from Ontario to Chicago?

There are 5 operators available for flights from Ontario to Chicago as of January 2026.

How old do you have to be to fly from Ontario to Chicago?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Ontario to Chicago.

What documentation or ID do you need to fly to Chicago?

The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

C$ 135 Cheap Flights from Ontario to Chicago in 2026

1 adult

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Find the cheapest flights from Ontario to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:15 a.m. - 10:05 a.m.

YTZ

MDW

1h 50mdirect

4:15 p.m. - 6:57 p.m.

MDW

YTZ

1h 42mdirect

C$ 249Multiple Airlines

Fri, 20 Feb - Sun, 22 Feb

9:00 p.m. - 10:05 p.m.

YYZ

ORD

2h 05mdirect

11:15 a.m. - 2:01 p.m.

ORD

YYZ

1h 46mdirect

C$ 251Lufthansa

Thu, 5 Feb - Sun, 8 Feb

11:30 a.m. - 12:25 p.m.

YYZ

ORD

1h 55mdirect

11:50 a.m. - 5:40 p.m.

ORD

YYZ

4h 50m1 stop

C$ 254American Airlines

Tue, 3 Feb - Tue, 10 Feb

11:00 a.m. - 11:50 a.m.

YTZ

MDW

1h 50mdirect

12:45 p.m. - 3:27 p.m.

MDW

YTZ

1h 42mdirect

C$ 254Porter Airlines

Sat, 21 Feb - Sat, 28 Feb

11:00 a.m. - 11:50 a.m.

YTZ

MDW

1h 50mdirect

11:00 a.m. - 1:42 p.m.

MDW

YTZ

1h 42mdirect

C$ 255Porter Airlines

Sat, 31 Jan - Mon, 2 Feb

3:59 p.m. - 9:32 p.m.

YUL

ORD

6h 33m1 stop

6:40 a.m. - 10:56 p.m.

ORD

YUL

15h 16m1 stop

C$ 260American Airlines

Mon, 9 Feb - Sun, 15 Feb

4:45 p.m. - 6:51 p.m.

YUL

ORD

3h 06mdirect

1:00 p.m. - 7:48 p.m.

ORD

YUL

5h 48m1 stop

C$ 262United Airlines

Fri, 6 Feb - Mon, 9 Feb

8:15 a.m. - 9:13 a.m.

YYZ

ORD

1h 58mdirect

8:00 a.m. - 10:40 a.m.

ORD

YYZ

1h 40mdirect

C$ 265Air Canada

Fri, 27 Feb - Sun, 1 Mar

6:40 p.m. - 7:40 p.m.

YYZ

ORD

2h 00mdirect

8:40 p.m. - 11:15 p.m.

ORD

YYZ

1h 35mdirect

C$ 266Air Canada

Fri, 30 Jan - Mon, 2 Feb

3:00 p.m. - 8:13 p.m.

YUL

ORD

6h 13m1 stop

7:10 a.m. - 1:28 p.m.

ORD

YUL

5h 18m1 stop

C$ 269United Airlines

Fri, 6 Feb - Tue, 10 Feb

Lufthansa flights from Region of Ontario to Chicago

Our best Lufthansa deals on Region of Ontario to Chicago flight tickets

Lufthansa

5 Feb

YYZ9:00 p.m.Toronto Pearson Intl

2h 05m

ORD10:05 p.m.Chicago O'Hare Intl

8 Feb

ORD11:15 a.m.Chicago O'Hare Intl

1h 46m

YYZ2:01 p.m.Toronto Pearson Intl

C$ 251

Find similar

Lufthansa

5 Feb

YYZ9:00 a.m.Toronto Pearson Intl

2h 06m

ORD10:06 a.m.Chicago O'Hare Intl

8 Feb

ORD6:28 p.m.Chicago O'Hare Intl

1h 53m

YYZ9:21 p.m.Toronto Pearson Intl

C$ 258

Find similar

Lufthansa

5 Feb

YUL7:00 a.m.Montreal Pierre Elliott Trudeau Intl

6h 05m

1 stop

ORD12:05 p.m.Chicago O'Hare Intl

8 Feb

ORD5:52 p.m.Chicago O'Hare Intl

2h 25m

YUL9:17 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 263

Find similar

Delta flights from Region of Ontario to Chicago

Our best Delta deals on Region of Ontario to Chicago flight tickets

Delta

4 Feb

YYZ6:06 a.m.Toronto Pearson Intl

5h 49m

1 stop

ORD10:55 a.m.Chicago O'Hare Intl

11 Feb

ORD6:50 a.m.Chicago O'Hare Intl

3h 30m

1 stop

YYZ11:20 a.m.Toronto Pearson Intl

C$ 285

Find similar

Delta

5 Feb

YYZ10:05 a.m.Toronto Pearson Intl

4h 08m

1 stop

ORD1:13 p.m.Chicago O'Hare Intl

9 Feb

ORD10:35 a.m.Chicago O'Hare Intl

4h 37m

1 stop

YYZ4:12 p.m.Toronto Pearson Intl

C$ 298

Find similar

Delta

3 Feb

YUL1:02 p.m.Montreal Pierre Elliott Trudeau Intl

9h 03m

1 stop

ORD9:05 p.m.Chicago O'Hare Intl

10 Feb

ORD2:50 p.m.Chicago O'Hare Intl

8h 00m

1 stop

YUL11:50 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 299

Find similar

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 20/2

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Sun 22/2

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 249

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 5/2

9:00 p.m.-10:05 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Sun 8/2

11:15 a.m.-2:01 p.m.

Nonstop1h 46m

C$ 251

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 3/2

11:30 a.m.-12:25 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Tue 10/2

11:50 a.m.-5:40 p.m.

1 stop4h 50m

C$ 254

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 21/2

11:00 a.m.-11:50 a.m.

Nonstop1h 50m

Chicago Midway

Sat 28/2

12:45 p.m.-3:27 p.m.

Nonstop1h 42m

C$ 254

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 31/1

11:00 a.m.-11:50 a.m.

Nonstop1h 50m

Chicago Midway

Mon 2/2

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 255

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Mon 9/2

3:59 p.m.-9:32 p.m.

1 stop6h 33m

Chicago O'Hare Intl

Sun 15/2

6:40 a.m.-10:56 p.m.

1 stop15h 16m

C$ 260

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 6/2

4:45 p.m.-6:51 p.m.

Nonstop3h 06m

Chicago O'Hare Intl

Mon 9/2

1:00 p.m.-7:48 p.m.

1 stop5h 48m

C$ 262

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 27/2

8:15 a.m.-9:13 a.m.

Nonstop1h 58m

Chicago O'Hare Intl

Sun 1/3

8:00 a.m.-10:40 a.m.

Nonstop1h 40m

C$ 265

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 30/1

6:40 p.m.-7:40 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Mon 2/2

8:40 p.m.-11:15 p.m.

Nonstop1h 35m

C$ 266

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 6/2

3:00 p.m.-8:13 p.m.

1 stop6h 13m

Chicago O'Hare Intl

Tue 10/2

7:10 a.m.-1:28 p.m.

1 stop5h 18m

C$ 269

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Region of Ontario to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Chicago?

The month of June is another great option to travel to Chicago, with average flight prices from Region of Ontario averaging around C$ 310.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 582. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around C$ 1,037. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

What is the cheapest time of day to depart on your flight to Chicago?

In the evening is the cheapest time of day to fly from Region of Ontario to Chicago when you can find flight prices for as low as C$ 633. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,080 per ticket.

What is the cheapest Ontario to Chicago flight route?

Fly from Toronto Island to Chicago Midway for the best Ontario - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Region of Ontario when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 395 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Region of Ontario for as low as C$ 269 on momondo.

What cabin class options are available on Ontario to Chicago flights?

There are 4 cabin classes available to choose from on Ontario to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Region of Ontario to Chicago flights?

No. A direct flight is the cheapest option for a flight between Region of Ontario to Chicago.

Cheap Region of Ontario to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Region of Ontario to Chicago

Best price found	C$ 197
Fastest flight time	1h 49m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Region of Ontario in the past 72 hours is C$ 197. The best round-trip flight deal from Region of Ontario to Chicago found on momondo in the last 72 hours is C$ 287.

The fastest flight from Region of Ontario to Chicago takes 1h 49m

Direct flights go from Region of Ontario to Chicago every day.

There are 3 airports in Chicago. From Region of Ontario there are direct flights to Chicago Midway (MDW).

Search flight deals

When did momondo last update prices for flights from Ontario to Chicago?
Prices for flights from Ontario to Chicago were last updated today.
How many operators does momondo search for flights from Ontario to Chicago?
There are 5 operators available for flights from Ontario to Chicago as of January 2026.
How old do you have to be to fly from Ontario to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Ontario to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Region of Ontario to Chicago?
Based on momondo bookings for flights between Region of Ontario and Chicago, the leading plane model is De Havilland (Bombardier) DHC-8-400 Dash 8Q, making up 14.36% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 12.58%, Embraer 195 E2 with 10.84%, and Embraer 170 with 9.13%.

Best airlines flying from Region of Ontario to Chicago

Compare and see reviews for airlines that fly from Region of Ontario to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Porter Airlines	PriceFrom C$ 195	Free Cancellation	Rating 8.0 406 reviews	Search Porter Airlines flights
Air Canada	PriceFrom C$ 256	Free Cancellation	Rating 7.1 10,602 reviews	Search Air Canada flights
American Airlines	PriceFrom C$ 259	Free Cancellation	Rating 7.2 11,093 reviews	Search American Airlines flights
United Airlines	PriceFrom C$ 262	Free Cancellation	Rating 7.4 9,139 reviews	Search United Airlines flights
WestJet	PriceFrom C$ 368	Free Cancellation	Rating 7.2 3,235 reviews	Search WestJet flights

Munster

Hammond

Merrillville

Why use momondo?

Why should I use momondo to find a flight deal from Ontario to Chicago?

Finding the right flight to Chicago from Ontario is quick and easy when you have a range of options in front of you, from reputable agents and recognizable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Ontario to Chicago with flexible booking policies on momondo?

Flights from Ontario to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Ontario to Chicago?

Once all potential Ontario to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Ontario to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Ontario and alert you when they change.